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On the Phenyliodine(III)-Bis(trifluoroacetate)-Mediated Olefin Amidohydroxylation Reaction

✍ Scribed by Imanol Tellitu; Andrea Urrejola; Sonia Serna; Isabel Moreno; M. Teresa Herrero; Esther Domínguez; Raul SanMartin; Arkaitz Correa

Book ID
102171490
Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
192 KB
Volume
2007
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

When appropriately substituted amides are treated with PIFA in a non‐nucleophilic solvent like trifluoroethanol, a stable N‐acylnitrenium ion is generated. If under such conditions a C=C double bond is present in the molecule, an intramolecular cyclization process takes place in an exo mode with additional generation of a hydroxy group at the terminal position of the original olefin moiety to render a series of pyrrolidine and piperidine derivatives. In this paper, proofs are offered to conclude that, according to our assumption, an ionic mechanism rather than a radical one must be considered. Additionally, a study of the scope of this cyclization protocol is conducted using substrates with different substituents either on the amidic nitrogen or all along the carbon chain.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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✍ Arkaitz Correa; Imanol Tellitu; Esther Dominguez; Raul SanMartin 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 19 KB 👁 2 views

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